2-Fluoro-3-methoxyphenylboronic acid → 4-Fluoro-1-(2'-fluoro-3'-methoxybiphenyl-3-yl)-1-(pyridin-4-yl)-1H-isoindol-3-amine

HRID 1662235Notes

Reaction equation

HRID 1662235 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2([C:19]3[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=3)[C:16]3[C:11](=[C:12]([F:17])[CH:13]=[CH:14][CH:15]=3)[C:10]([NH2:18])=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[F:25][C:26]1[C:31]([O:32][CH3:33])=[CH:30][CH:29]=[CH:28][C:27]=1B(O)O>>[F:17][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:11]=1[C:10]([NH2:18])=[N:9][C:8]2([C:4]1[CH:3]=[C:2]([C:27]2[CH:28]=[CH:29][CH:30]=[C:31]([O:32][CH3:33])[C:26]=2[F:25])[CH:7]=[CH:6][CH:5]=1)[C:19]1[CH:20]=[CH:21][N:22]=[CH:23][CH:24]=1

Participants

3

Reactant 2

HCID 49857442-Fluoro-3-methoxyphenylboronic acidHCID 585794851-(3-bromophenyl)-4-fluoro-1-(pyridin-4-yl)-1H-isoindol-3-amine

Product 1

HCID 462062934-Fluoro-1-(2'-fluoro-3'-methoxybiphenyl-3-yl)-1-(pyridin-4-yl)-1H-isoindol-3-amineYield 28%

Procedure

The title compound was synthesized as described for Example 1 in 28% yield, starting from 1-(3-bromophenyl)-4-fluoro-1-(pyridin-4-yl)-1H-isoindol-3-amine (0.096 g, 0.25 mmol) and 2-fluoro-3-methoxybenzeneboronic acid (0.047 g, 0.28 mmol): 1H NMR (DMSO-d6) δ ppm 8.50-8.44 (m, 2 H) 7.65-7.60 (m, 1 H) 7.58-7.49 (m, 1 H) 7.45-7.37 (m, 3 H) 7.36-7.24 (m, 4 H) 7.22-7.11 (m, 2 H) 6.96-6.90 (m, 1 H) 6.64 (br. s., 2H) 3.85 (s, 3 H), MS (ES+) m/z 428 [M+1]+.

Sources & evidence

ORD record
ord-fc39b28211ef491688ddffe5d6594446
Source dataset
uspto-grants-2011_10
Patent number
US08030500B2

Reaction notes

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